CuO-catalyzed conversion of arylacetic acids into aromatic nitriles with K4Fe(CN)6 as the nitrogen source

AbstractA new and effective method was developed for the synthesis of aromatic nitriles from arylacetic acids by using NaNO2 as the nitrogen source and Fe(OTf)3 as the promoter at 50 °C. A series of arylacetic acids underwent this transformation to give the targeted products in yields of 51–90%. Because of the mild conditions, the reaction is compatible with a broad range of functional groups, including ester, carboxy, hydroxy, acetamido, halo, nitro, cyano, methoxy, and even highly reactive formyl groups.

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Direct Conversion of Benzyl Ethers into Aryl Nitriles

Synlett ◽

10.1055/s-0037-1611062 ◽

2018 ◽

Vol 29 (18) ◽

pp. 2444-2448 ◽

Cited By ~ 11

Author(s):

Yun-Lai Ren ◽

Jianji Wang ◽

Xinzhe Tian ◽

Fangping Ren ◽

Xinqiang Cheng ◽

...

Keyword(s):

Nitrogen Source ◽

Direct Method ◽

Direct Conversion ◽

Aromatic Nitriles ◽

Organic Syntheses ◽

Aryl Nitriles ◽

Benzyl Ethers ◽

Hydroxy Groups ◽

A Direct Method

A direct method was developed for the conversion of benzyl ethers into aryl nitriles by using NH4OAc as the nitrogen source and oxygen as the terminal oxidant with catalysis by TEMPO/HNO3; the method is valuable for both the synthesis of aromatic nitriles and for the deprotection of ether-protected hydroxy groups to form nitrile groups in multistep organic syntheses.

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ChemInform Abstract: An Aerobic Cu-Mediated Practical Approach to Aromatic Nitriles Using Cyanide Anions as the Nitrogen Source.

ChemInform ◽

10.1002/chin.201647085 ◽

2016 ◽

Vol 47 (47) ◽

Author(s):

Lijun Gu ◽

Cheng Jin ◽

Hongtao Zhang ◽

Jiyan Liu ◽

Ganpeng Li Ganpeng Li ◽

...

Keyword(s):

Nitrogen Source ◽

Practical Approach ◽

Aromatic Nitriles

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An aerobic Cu-mediated practical approach to aromatic nitriles using cyanide anions as the nitrogen source

Organic & Biomolecular Chemistry ◽

10.1039/c6ob01269h ◽

2016 ◽

Vol 14 (28) ◽

pp. 6687-6690 ◽

Cited By ~ 5

Author(s):

Lijun Gu ◽

Cheng Jin ◽

Hongtao Zhang ◽

Jiyan Liu ◽

Ganpeng Li Ganpeng Li ◽

...

Keyword(s):

Nitrogen Source ◽

Practical Approach ◽

Methyl Ketones ◽

Aromatic Nitriles ◽

Aryl Methyl

A copper-catalyzed cyanation of aryl methyl ketones using cyanide anions as the nitrogen source was developed. The reaction showed a broad substrate scope with moderate to excellent yields.

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Sulfur-Mediated Decarboxylative Coupling of 2-Nitrobenzyl Alcohols and Arylacetic Acids

Synlett ◽

10.1055/s-0040-1707113 ◽

2020 ◽

Vol 31 (11) ◽

pp. 1112-1116

Author(s):

Tung T. Nguyen ◽

Nam T. S. Phan ◽

Khang X. Nguyen ◽

Duyen K. Nguyen ◽

Phuc H. Pham ◽

...

Keyword(s):

Transition Metals ◽

Nitrogen Source ◽

Elemental Sulfur ◽

New Method ◽

Complex Structures ◽

Reaction Conditions ◽

Mild Conditions ◽

Decarboxylative Coupling ◽

Arylacetic Acids

We report a new method for the synthesis of substituted quinazolines by the condensation of 2-nitrobenzyl alcohols with arylacetic acids. The transformation requires the use of urea as a nitrogen source, elemental sulfur as a promoter, DABCO as a base, and DMSO as a solvent. Functionalities such as chloro, fluoro, trifluoromethyl, thienyl, and indolyl groups were all compatible with the reaction conditions. Because our method uses stable simple substrates to obtain the N,N-heterocycles in the absence of transition metals, it offers a potential pathway for preparing complex structures under mild conditions.

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